Aniline → N-Phenylmaleimide

HRID 1586855Notes

Reaction equation

[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1C=CC=CC=1>[C:9]1([N:8]2[C:4](=[O:5])[CH:3]=[CH:2][C:1]2=[O:7])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 10 °C

Procedure

N-phenylmaleimide was synthesized in accordance with a method described in "Organic Synthesis", Vol.41, page 93. That is, 196 parts of maleic anhydride and 2,000 parts of benzene were charged into a four-necked flask. 186 parts of aniline dissolved in 200 parts of benzene were added dropwise to the resulting solution at 25° C. over one hour. The resulting product was cooled to 10° C. and crystals thus formed were filtered off and dried in vacuo to give 370 parts of a pale yellow solid substance. 316 parts of the produced pale yellow substance, 65 parts of anhydrous sodium acetate and 670 parts of acetic anhydride were charged into a flask fitted with a stirrer and a reflux cooler and heated gradually over an hour. Stirring was continued for one hour while the temperature was maintained at 100° C. The resulting product was poured into ice water to precipitate crystals. The crystals were filtered, washed with petroleum ether and dried to give 220 parts of yellow crystals. The melting point and the purity by liquid chromatography of the produced crystals were measured and found to be 88° C. and 97.5%, respectively. The produced maleimide compounds are shown in Table 1-1.

Workup

customdescribed in "Organic Synthesis", Vol.41, page 93
additionwere added dropwise to the resulting solution at 25° C. over one hour
customcrystals thus formed
filtrationwere filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-075b1c3620e44cec904cd743dfdea1c7
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05216047

Reaction notes

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